CA2371540C - Crystallising polyether polyols, a method for producing them and use of the same - Google Patents

Crystallising polyether polyols, a method for producing them and use of the same Download PDF

Info

Publication number: CA2371540C
Authority: CA; Canada
Prior art keywords: crystallising; propylene oxide; molecular weight; average molecular; polyol
Prior art date: 1999-04-28
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

CA002371540A

Other languages

English (en)

French (fr)

Other versions

CA2371540A1 (en

Inventor

Walter Schafer

Jorg Hofmann

Pramod Gupta

Pieter Ooms

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer AG

Original Assignee

Bayer AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1999-04-28

Filing date

2000-04-18

Publication date

2008-07-08

2000-04-18 Application filed by Bayer AG filed Critical Bayer AG

2000-11-09 Publication of CA2371540A1 publication Critical patent/CA2371540A1/en

2008-07-08 Application granted granted Critical

2008-07-08 Publication of CA2371540C publication Critical patent/CA2371540C/en

2020-04-18 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

229920005862 polyol Polymers 0.000 title claims abstract description 66
150000003077 polyols Chemical class 0.000 title claims abstract description 66
229920000570 polyether Polymers 0.000 title claims abstract description 52
239000004721 Polyphenylene oxide Substances 0.000 title claims abstract description 51
238000004519 manufacturing process Methods 0.000 title claims abstract description 13
239000003054 catalyst Substances 0.000 claims abstract description 37
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims abstract description 29
150000002924 oxiranes Chemical class 0.000 claims abstract description 20
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 17
150000001875 compounds Chemical class 0.000 claims abstract description 14
229920002635 polyurethane Polymers 0.000 claims abstract description 12
239000004814 polyurethane Substances 0.000 claims abstract description 12
239000011701 zinc Substances 0.000 claims abstract description 12
-1 alkoxy compound Chemical class 0.000 claims abstract description 11
229910052725 zinc Inorganic materials 0.000 claims abstract description 11
239000000463 material Substances 0.000 claims abstract description 9
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical group [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims abstract description 5
238000000034 method Methods 0.000 claims description 7
239000007795 chemical reaction product Substances 0.000 claims 1
229920001228 polyisocyanate Polymers 0.000 claims 1
239000005056 polyisocyanate Substances 0.000 claims 1
229920005830 Polyurethane Foam Polymers 0.000 abstract description 2
238000000576 coating method Methods 0.000 abstract description 2
239000000806 elastomer Substances 0.000 abstract description 2
239000011496 polyurethane foam Substances 0.000 abstract description 2
229920003225 polyurethane elastomer Polymers 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
238000006243 chemical reaction Methods 0.000 description 17
239000000047 product Substances 0.000 description 15
239000000543 intermediate Substances 0.000 description 13
229910052751 metal Inorganic materials 0.000 description 13
239000002184 metal Substances 0.000 description 13
239000004411 aluminium Substances 0.000 description 12
229910052782 aluminium Inorganic materials 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 9
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 8
239000000243 solution Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 8
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
239000003999 initiator Substances 0.000 description 6
239000004793 Polystyrene Substances 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
239000000203 mixture Substances 0.000 description 5
229920002223 polystyrene Polymers 0.000 description 5
239000001117 sulphuric acid Substances 0.000 description 5
235000011149 sulphuric acid Nutrition 0.000 description 5
238000005406 washing Methods 0.000 description 5
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 4
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
238000006555 catalytic reaction Methods 0.000 description 4
239000012043 crude product Substances 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
229910001854 alkali hydroxide Inorganic materials 0.000 description 3
150000008044 alkali metal hydroxides Chemical class 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
229920001451 polypropylene glycol Polymers 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
230000000707 stereoselective effect Effects 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000002585 base Substances 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
238000000926 separation method Methods 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
TURGQPDWYFJEDY-UHFFFAOYSA-N 1-hydroperoxypropane Chemical compound CCCOO TURGQPDWYFJEDY-UHFFFAOYSA-N 0.000 description 1
HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
239000003463 adsorbent Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical class [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
229920001400 block copolymer Polymers 0.000 description 1
229910052792 caesium Inorganic materials 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
RKBAPHPQTADBIK-UHFFFAOYSA-N cobalt;hexacyanide Chemical compound [Co].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] RKBAPHPQTADBIK-UHFFFAOYSA-N 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
230000000536 complexating effect Effects 0.000 description 1
239000000470 constituent Substances 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
235000013681 dietary sucrose Nutrition 0.000 description 1
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
UZZWBUYVTBPQIV-UHFFFAOYSA-N dme dimethoxyethane Chemical compound COCCOC.COCCOC UZZWBUYVTBPQIV-UHFFFAOYSA-N 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000006260 foam Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
235000011167 hydrochloric acid Nutrition 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000003446 ligand Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920005606 polypropylene copolymer Polymers 0.000 description 1
239000011527 polyurethane coating Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
229910052712 strontium Inorganic materials 0.000 description 1
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
239000000126 substance Substances 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
239000000725 suspension Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000012855 volatile organic compound Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
- C08G65/269—Mixed catalyst systems, i.e. containing more than one reactive component or catalysts formed in-situ
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2101/00—Manufacture of cellular products
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2250/00—Compositions for preparing crystalline polymers

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Polyethers (AREA)
Polyurethanes Or Polyureas (AREA)
Processing And Handling Of Plastics And Other Materials For Molding In General (AREA)
Processes Of Treating Macromolecular Substances (AREA)
Paints Or Removers (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Steroid Compounds (AREA)
Crystals, And After-Treatments Of Crystals (AREA)
Polyesters Or Polycarbonates (AREA)

CA002371540A 1999-04-28 2000-04-18 Crystallising polyether polyols, a method for producing them and use of the same Expired - Fee Related CA2371540C (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE19919267A DE19919267A1 (de)	1999-04-28	1999-04-28	Kristallisierende Polyetherpolyole, ein Verfahren zu deren Herstellung sowie deren Verwendung
DE19919267.7		1999-04-28
PCT/EP2000/003495 WO2000066648A1 (de)	1999-04-28	2000-04-18	Kristallisierende polyetherpolyole, ein verfahren zu deren herstellung sowie deren verwendung

Publications (2)

Publication Number	Publication Date
CA2371540A1 CA2371540A1 (en)	2000-11-09
CA2371540C true CA2371540C (en)	2008-07-08

Family

ID=7906131

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002371540A Expired - Fee Related CA2371540C (en)	1999-04-28	2000-04-18	Crystallising polyether polyols, a method for producing them and use of the same

Country Status (20)

Country	Link
US (1)	US6569981B1 (id)
EP (1)	EP1177237B1 (id)
JP (1)	JP4896296B2 (id)
KR (1)	KR100558233B1 (id)
CN (1)	CN1117789C (id)
AT (1)	ATE274015T1 (id)
AU (1)	AU4296300A (id)
BR (1)	BR0010066B1 (id)
CA (1)	CA2371540C (id)
CZ (1)	CZ20013850A3 (id)
DE (2)	DE19919267A1 (id)
ES (1)	ES2226820T3 (id)
HK (1)	HK1046418B (id)
HU (1)	HUP0200943A2 (id)
ID (1)	ID30442A (id)
MX (1)	MXPA01010932A (id)
PL (1)	PL351610A1 (id)
RU (1)	RU2001132153A (id)
TW (1)	TW527376B (id)
WO (1)	WO2000066648A1 (id)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN101506268B (zh) *	2006-08-31	2012-09-05	旭硝子株式会社	聚醚类的精制方法
ES2881179T3 (es) *	2010-12-27	2021-11-29	Dow Global Technologies Llc	Polimerización de óxido de alquileno usando un complejo catalítico de cianuro de metal doble y un compuesto metálico de magnesio, metal del grupo 3-grupo 15 o metal de la serie de lantánidos

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE566583A (id)	1957-04-08
DE1720337A1 (de)	1967-12-27	1971-06-09	Basf Ag	Verfahren zur Herstellung von hochmolekularen Polyaethern aus Epoxyden
JPS4812080B1 (id) *	1969-10-20	1973-04-18
JPS495237B1 (id) *	1970-01-07	1974-02-06
JPS495637B1 (id) *	1970-03-19	1974-02-08
JPS4917440B1 (id) *	1970-09-08	1974-04-30
US4962281A (en)	1985-12-13	1990-10-09	The Dow Chemical Company	Synthesis of stereoregular poly(propylene oxide)
DE19709031A1 (de) *	1997-03-06	1998-09-10	Basf Ag	Verfahren zur Herstellung von Doppelmetallcyanidkatalysatoren
DE19748359A1 (de) *	1997-11-03	1999-05-06	Bayer Ag	Verfahren zur Herstellung teilkristalliner Polyetherpolyole

1999
- 1999-04-28 DE DE19919267A patent/DE19919267A1/de not_active Withdrawn
2000
- 2000-04-18 US US10/030,489 patent/US6569981B1/en not_active Expired - Lifetime
- 2000-04-18 EP EP00922645A patent/EP1177237B1/de not_active Expired - Lifetime
- 2000-04-18 KR KR1020017013782A patent/KR100558233B1/ko not_active Expired - Fee Related
- 2000-04-18 JP JP2000615675A patent/JP4896296B2/ja not_active Expired - Fee Related
- 2000-04-18 CA CA002371540A patent/CA2371540C/en not_active Expired - Fee Related
- 2000-04-18 AU AU42963/00A patent/AU4296300A/en not_active Abandoned
- 2000-04-18 BR BRPI0010066-8A patent/BR0010066B1/pt not_active IP Right Cessation
- 2000-04-18 ES ES00922645T patent/ES2226820T3/es not_active Expired - Lifetime
- 2000-04-18 DE DE50007496T patent/DE50007496D1/de not_active Expired - Lifetime
- 2000-04-18 RU RU2001132153/04A patent/RU2001132153A/ru not_active Application Discontinuation
- 2000-04-18 HU HU0200943A patent/HUP0200943A2/hu unknown
- 2000-04-18 PL PL00351610A patent/PL351610A1/xx not_active Application Discontinuation
- 2000-04-18 CZ CZ20013850A patent/CZ20013850A3/cs unknown
- 2000-04-18 ID IDW00200102350A patent/ID30442A/id unknown
- 2000-04-18 AT AT00922645T patent/ATE274015T1/de not_active IP Right Cessation
- 2000-04-18 HK HK02107962.7A patent/HK1046418B/zh not_active IP Right Cessation
- 2000-04-18 MX MXPA01010932A patent/MXPA01010932A/es unknown
- 2000-04-18 WO PCT/EP2000/003495 patent/WO2000066648A1/de not_active Ceased
- 2000-04-18 CN CN00806680A patent/CN1117789C/zh not_active Expired - Lifetime
- 2000-04-21 TW TW089107513A patent/TW527376B/zh not_active IP Right Cessation

Also Published As

Publication number	Publication date
KR20020003872A (ko)	2002-01-15
JP4896296B2 (ja)	2012-03-14
ID30442A (id)	2001-12-06
HK1046418A1 (en)	2003-01-10
CA2371540A1 (en)	2000-11-09
CZ20013850A3 (cs)	2002-02-13
US6569981B1 (en)	2003-05-27
HUP0200943A2 (en)	2002-07-29
ES2226820T3 (es)	2005-04-01
WO2000066648A1 (de)	2000-11-09
RU2001132153A (ru)	2003-09-10
CN1349548A (zh)	2002-05-15
JP2002543255A (ja)	2002-12-17
BR0010066A (pt)	2002-01-15
EP1177237B1 (de)	2004-08-18
KR100558233B1 (ko)	2006-03-10
AU4296300A (en)	2000-11-17
DE50007496D1 (de)	2004-09-23
PL351610A1 (en)	2003-05-05
EP1177237A1 (de)	2002-02-06
BR0010066B1 (pt)	2010-06-15
DE19919267A1 (de)	2000-11-02
MXPA01010932A (es)	2002-06-21
HK1046418B (zh)	2004-05-07
TW527376B (en)	2003-04-11
ATE274015T1 (de)	2004-09-15
CN1117789C (zh)	2003-08-13

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Date	Code	Title	Description
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2017-05-30	MKLA	Lapsed	Effective date: 20170418

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